A few years ago, the Yankees and Cubs were in opposite points of contention. The Yankees were reluctant sellers, trading away key expiring contracts to jumpstart a rebuild into the next generation of Yankees teams. The Cubs were championship favorites, seeking to add insurance for a curse-breaking title push. Both teams found common ground, and they made a deal that worked out fantastically for each side.
Now the situation is different. The Yankees have been a team that’s come close, but not close enough to a World Series title, while the Cubs have stagnated from their peak in 2016.